Currently on the road with Gilbert, Ray admits that YouTube has become a big part of his setlist strategy.

"I try to go back and watch sets -- like, how does [Kenny] Chesney set up his setlist, how does Garth [Brooks] set up his setlist, as far as a movement goes," he explains. "Honestly, I go to YouTube and look these guys up and see how they formed their setlist."

During his shows with Gilbert, Ray has 35 minutes, so he tries to "cram as much music as I can" into that time frame; however, he also tries to be smart and not just play, play, play.

"You try to play as much music as you can, but that also doesn't take away from the personal connection with the audience," he notes. "We just try to make a setlist with a good flow."

Ray has been on the road since he was 16 -- and he comes from a family of musicians -- so he's confident in his abilities to read and connect with a crowd. That's also helped him pick new singles; "a big part of that is crowd reaction," he says of selecting which songs to send to radio, including his newest single, "Think a Little Less."

But after he's finished opening for a band, Ray doesn't pack it up in the bus for the evening; rather, he watches every single show -- gladly.

"All my guys -- we watch every show, we don't miss a night," he confesses. "It's always different. They've been where we are, so we try to learn from them now ... I used to cover Brantley's songs when I was in high school. So just being there, I'm like, 'I get to tour with Brantley, and I get a free show every night.' It's awesome."

"I'm a huge Darius fan. I was a huge Hootie [and the Blowfish] fan," Ray exclaims. "He is just an iconic artist in country music -- and generally in music. Darius Rucker is the guy that will be remembered forever."

He adds, "Fingers crossed, hopefully we'll do a Hootie song at the end of the night."

Even though Ray's touring schedule is busy, his sights are set on his next album. He's already begun writing and reveals that he's been on the phone with publishers to listen to outside songs.